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Pender's Blog by Lee Pender, RCPU Editor

Could an Underdog Microsoft Become Cool?

Apple is cool. Do we have to try and quantify that? Nah. You don't have to be cool to know who's cool. Were you one of the cool kids in high school? If not, did you know who was? Well, that's our point. We at RCPU are not cool, but we know that Apple is cool, and maybe Google is, too.

Microsoft is not. Never has been, really. One reason is that Microsoft has long been a bully, a company perceived (and probably not inaccurately) to have ripped off a lot of other vendors in its quest to dominate the technology industry. People still love to read about this stuff. The bitterness toward Microsoft is still strong. Doug Barney's recent Redmondmag.com story on the "10 Technologies Microsoft 'Borrowed'" has racked up an enormous number of hits (not to give away our trade secrets or anything).

Bullies are feared, maybe even respected -- but they're not cool. And cool matters in the consumer-heavy world of smartphones and tablets Microsoft so desperately wants to crack. Logos and labels are critical in that world, and Microsoft's is more likely to elicit a roll of the eyes from the in-crowd than it is a nod of respect. Apple's apple, on the other hand, is the gold standard of techie smugness and self-satisfaction.

Things might be changing, though, slowly, bit by bit. While digging around for articles to link to for another entry, we ran across this post from TechCrunch and couldn't help but notice what one of the user commenters had to say: "I strangely find myself rooting for Microsoft. They are the good guys now. Go Microsoft! You can do it!"

That sentiment got 99 "likes" on Facebook (at last count) and a couple of comments in support. It offers a tiny glimpse into how the least-cool vendor since IBM in the '80s (also a victim of Apple's swagger -- partially) can reposition itself in the consumer mind. Microsoft is the underdog now, at least in the kingdom of tablets and phones over which Apple and Google are currently fighting for control. And underdogs are almost always cool.

Think about it. Apple isn't the scrappy little guy anymore. It's not Avis or the pre-2004 Boston Red Sox. It is, in fact, more like the post-2004 Boston Red Sox, just another wealthy franchise that crushes competitors under its cleats and elicits relatively little sympathy from neutrals. Steve Jobs is brilliant but as a public figure is pretty difficult to like. Apple's hipster image can be overbearing, to say the least.

Plus (and this is very important), Apple is bigger than Microsoft now. Steve (Jobs) got the loot after all, and it doesn't really matter how much market share Mac has compared to Windows when the world has moved on to obsessing over smaller devices -- markets in which Apple is either the clear leader (tablets) or a major contender (smartphone operating systems). Those brilliant Mac Guy ads from a few years ago would seem awkward and incongruous now. The tables have turned.

Then there's Google, which is kind of mysterious and creepy. Is Google cool? Well, Android-based phones certainly sell well, but that might have something to do with their broad-based availability and the ability of carriers to offer them with reasonably priced plans. (Full disclosure: Your editor has an Android phone and really likes it.) Other than that, though, Google is kind of utilitarian, synonymous with search and big in the cloud but not necessarily cool.

IBM is the antithesis of cool, but it was briefly bigger that Microsoft recently (and might be again), which only helps the case for cool in Redmond. Sure, Microsoft has been a bully over the years. Yeah, Windows was and probably still is the cheese quesadilla appetizer to Mac's foie gras on toast points. But in this new world of little devices and touchscreens, Microsoft is the underdog. In fact, it's way, way behind its competitors. And in the technology industry, Microsoft isn't the alpha dog anymore. It's the beta, or maybe even the, um, third (our Greek is bad -- gamma?) dog. Microsoft should remind people of that every chance it gets.

Yes, that's right. Microsoft should go against every instinct its executives seem to have and every impression it has ever tried to deliver and make itself into the blue-collar, hard-working scrapper just trying to get a foothold among the evil giants of the handheld game. It has happened before. Let's stick with sports here: The Dallas Cowboys in the early '90s, the Boston Celtics a few years ago, even the hated (and evil) New York Yankees back in the mid-'90s reinvented themselves not so much as empires reborn but as interlopers into games somebody else was dominating at the time. They all came to dominate eventually (and once again engender tons of hatred, but that's the price of being on top, where everybody wants to be). Can Microsoft do the same? Maybe not, but it can and should try.

The message is this: If you're sitting in a coffee shop with a Microsoft Windows Phone 7 phone or Windows 8 tablet (as soon as there's a Windows 8 tablet to sit with), you're not a bandwagon fan surrendering to a nasty corporate force and falling in with the broad swath of sheep-like consumers. Oh, no. You're a rebel, part of the resistance, a game changer and a trendsetter. You're daring to shun Steve Jobs and Google for something new, something really different, something not everybody has the guts to buy.

You're not a PC. You're a Windows handheld device. You're a little out there, a little mysterious without being creepy. The iPad minions and Android lemmings are the sheeple. You're...cool. People want to be like you. You know it, and they know it. Will Microsoft ever know it? We kind of doubt it, but we also kind of hope so.